A New Silicon Lewis Acid for Highly Enantioselective Mannich Reactions of Aliphatic Ketone-Derived Hydrazones

Gregory T. Notte and James L. Leighton
Department of Chemistry, Columbia University, New York, New York 10027
J. Am. Chem. Soc., 2008, 130 (21), pp 6676–6677
DOI: 10.1021/ja800830h
Publication Date (Web): April 30, 2008
Copyright © 2008 American Chemical Society

Abstract

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The first general method for the highly enantioselective Mannich reaction of aliphatic ketimines is reported. A new, second generation chiral silane Lewis acid has been developed that promotes the reaction between ketone-derived hydrazones and silyl ketene acetals, providing the β,β-disubstituted β-amino esters with good enantioselectivity even for the hydrazone derived from 2-butanone (methyl vs ethyl, 91% ee). Several examples are provided, including a reaction with a substituted (propanoate-derived) silyl ketene acetal.

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History

  • Published In Issue May 28, 2008
  • Article ASAPApril 30, 2008
  • Received: February 01, 2008

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